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Historic Opera House For Sale

101 S Main Winchester, KY 40391

101 S Main, Winchester, KY, 40391
$1,750,000
For Sale
Claim this Listing
$1,750,000

COMMERCIAL - Winchester, KY

Property Size20,548 SF
Lot Size0.23 Acres
Price / SF$85.17
AddedNov 10, 2023
Days on Market977
Last RefreshJul 14 at 10:06 pm

Property Features for 101 S Main

General Information

Property type
Commercial Sale
Property subtype
Office
Standard status
Active
APN
054-3218-001-00
Size
20,548 SF
Lot size
0.23 Acres

Utilities

Utilities
Water Available
Sewer type
Public Sewer

Building Details

Floors in Building
3
Building materials
Brick

Listing agent Gregory Leveridge License #215416

Listing office Block + Lot Homes 133 W Short St, Lexington, KY

Listing date Nov 10, 2023

MLS# 23021742

Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.


Investment Insights

Based on property information with market context.

Located in the heart of Downtown Winchester, the fully-restored historic Opera House at 101 S. Main Street functions in a multiple-use capacity. The property includes gallery space, a successful restaurant space operating for seven years, wedding event and reception space, and office space. The extensive renovation includes multiple commercial kitchens, an interior elevator, gracious entertainment spaces, hardwood floors, large windows, exposed brick, and functioning fireplaces. The Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. The property offers flexible layouts for various uses, including continuing the existing operations with lease-back potential from the owner-occupied Loma's restaurant. Located in an Opportunity Zone, Downtown Winchester offers grants for renovations and business development. The property benefits from the City of Winchester's investment in the neighboring High Side Improvement Project, which includes $5.5 million invested in new angled parking, new sidewalks and added ramps, enhancing downtown accessibility, as well as 13 new high-end apartments with 10 more in development. The property size is 20,548 square feet, situated on a 0.23-acre lot.

Key Highlights

  • Fully‑restored historic Opera House with multiple income streams.
  • Successful, established restaurant (Loma's) with potential leaseback option.
  • Prime downtown location in Winchester, KY.

Property Analytics

Property Profile Location Intelligence

Current Use by Public Records

Peoples Exchange Insurance Atm Peoples Exchange Bank Bank

Suggested Use

Dental Office Real Estate Agency HVAC Service Skin Care Clinic Spa & Massage Center Gym & Fitness Center Bakery Carpet & Flooring Store Auto Parts Store Nail Salon

Zoning and permitted uses should be independently verified with local authorities.

FAQs

What type of property is this?
Wedding venue - Fully-restored Opera House in Downtown Winchester with multiple uses.
Where is this wedding venue located?
The property is located at 101 S Main Winchester, KY.
What is the asking price?
The asking price for this property is $1,750,000.
What are key features of this property?
This property features: Fully‑restored historic Opera House with multiple income streams.; Successful, established restaurant (Loma's) with potential leaseback option.; Prime downtown location in Winchester, KY.
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